US3591501A - Lubricant containing a hydroxy-substituted phosphine oxide - Google Patents
Lubricant containing a hydroxy-substituted phosphine oxide Download PDFInfo
- Publication number
- US3591501A US3591501A US793879*A US3591501DA US3591501A US 3591501 A US3591501 A US 3591501A US 3591501D A US3591501D A US 3591501DA US 3591501 A US3591501 A US 3591501A
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- United States
- Prior art keywords
- hydroxy
- oxide
- substituted
- composition
- fluid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000000314 lubricant Substances 0.000 title abstract description 5
- -1 hydroxy-substituted phosphine oxide Chemical class 0.000 title description 18
- 239000012530 fluid Substances 0.000 abstract description 31
- 239000000203 mixture Substances 0.000 abstract description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 230000001050 lubricating effect Effects 0.000 description 6
- 229940059574 pentaerithrityl Drugs 0.000 description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 239000011574 phosphorus Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- YFPJFKYCVYXDJK-UHFFFAOYSA-N Diphenylphosphine oxide Chemical compound C=1C=CC=CC=1[P+](=O)C1=CC=CC=C1 YFPJFKYCVYXDJK-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 3
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- TVWTZAGVNBPXHU-FOCLMDBBSA-N dioctyl (e)-but-2-enedioate Chemical compound CCCCCCCCOC(=O)\C=C\C(=O)OCCCCCCCC TVWTZAGVNBPXHU-FOCLMDBBSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 239000010689 synthetic lubricating oil Substances 0.000 description 2
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 241000167854 Bourreria succulenta Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000005643 Pelargonic acid Substances 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 235000019693 cherries Nutrition 0.000 description 1
- 150000001925 cycloalkenes Chemical class 0.000 description 1
- ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 239000012969 di-tertiary-butyl peroxide Substances 0.000 description 1
- 239000012933 diacyl peroxide Substances 0.000 description 1
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- RZRNAYUHWVFMIP-HXUWFJFHSA-N glycerol monolinoleate Natural products CCCCCCCCC=CCCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-HXUWFJFHSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000005604 isopentanoic acids Chemical class 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000003879 lubricant additive Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000010688 mineral lubricating oil Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000005673 monoalkenes Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical group P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920013636 polyphenyl ether polymer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 231100000241 scar Toxicity 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 238000007514 turning Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/286—Esters of polymerised unsaturated acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
- C10M2223/061—Metal salts
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/043—Siloxanes with specific structure containing carbon-to-carbon double bonds
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/044—Siloxanes with specific structure containing silicon-to-hydrogen bonds
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/045—Siloxanes with specific structure containing silicon-to-hydroxyl bonds
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/046—Siloxanes with specific structure containing silicon-oxygen-carbon bonds
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/047—Siloxanes with specific structure containing alkylene oxide groups
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/048—Siloxanes with specific structure containing carboxyl groups
Definitions
- the invention relates to lubricant compositions, and in particular to lubricating compositions comprising an organic fluid of lubricating viscosity and a hydroxy-substituted organophosphine oxide, said composition having improved load carrying properties.
- an organic fluid composition comprising a major proportion of an organic fluid of lubricating viscosity and a minor proportion suflicient to impart load carrying properties thereto of a hydroxy-substituted organophosphine oxide.
- the hydroxy-substituted organophosphine oxide has the formula wherein R, R and R may be the same or different alkyl, cycloalkyl, aralkyl, aryl, alkaryl, and the substituted derivatives thereof, wherein the substituent may be a portion of the ring structure or attached to the alkyl or aryl groups or to either moiety in the alkaryl or aralkyl group, and contain atoms selected from the group consisting of nitrogen, oxygen, sulfur and halogen.
- R, R and R are selected from the group consisting of: (a) alkyl, cycloalkyl and heterocyclic groups containing from 1 to about 20 carbon atoms; (b) aryl, aralkyl and alkaryl groups containing a total of from 6 to about 30 carbon atoms; and (c) the substituted members of (a) and (b).
- the substituent is a member of the group consisting of halogen (chlorine, fluorine, bromine and iodine), hydroxy,
- heterocyclic group will contain a substituent from the group consisting of nitrogen, oxygen and sulfur, and the alkyl groups may contain such atoms as portions of the molecule between consecutive atoms in the chain.
- organophosphine oxides of this invention when incorporated with organic fluids, give lubricating compositions having good load carrying properties.
- the diorgano phosphonate used as the starting material for the secondary phosphine oxide may be prepared by reacting an alcohol or a phenol with phosphorus trichloride in the desired mole ratio.
- the diaryl phosphonates may be prepared by reacting together phenol, water or an alcohol, and phosphorus trichloride in accordance with the method disclosed in US. Pat. No. 3,329,742.
- the mole ratio of phenol to water or alcohol to phosphorus trichloride is 2 to 1 to 1, and the temperature is within the range of about 25 C. to about C.
- the hydroxy-substituted organophosphine oxides disclosed herein are eifective to impart load carrying properties to a variety of organic fluids having lubricating viscosity.
- organic fluids include, in addition to mineral oils such as naphthenic and parafiinic mineral oils, synthetic oils including hydrocarbon base fluids, glycol ether fluids, poly(organo) siloxane fluids, acetals, polyphenyl ethers, and the synthetic ester fluids produced from monohydric alcohols and polycarboxylic acids, or from polyhydric alcohols, such as trimethylolpropane and pentaerythritol, and carboxylic acids having up to about 20 carbon atoms.
- mineral oils such as naphthenic and parafiinic mineral oils
- synthetic oils including hydrocarbon base fluids, glycol ether fluids, poly(organo) siloxane fluids, acetals, polyphenyl ethers, and the synthetic ester fluids produced from monohydr
- the hydrocarbon base fluid there may be mentioned a polyolefinic fluid or a hydrogenated derivative thereof.
- One suitable fluid is similar to that disclosed and claimed in US. Pat. 3,149,178.
- the olefinic fluids are polymerized normal alphamonoolefins which are distilled to yield a. dimer fraction and a dimer-free fraction.
- the dimer-free fraction may be thereafter hydrogenated in the presence of a catalyst, such as boron trifluoride.
- a catalyst such as boron trifluoride.
- Other useful olefinic fluids may be prepared in accordance with US. Pat. 3,382,291.
- the poly(organo)siloxane fluids may be exemplified by those products obtained by reacting a polysiloxane containing the recurring unit and having a molecular weight of from about 500 to about 10,000 with an unsaturated compound containing at least one double bond; which compound adds to the H of the above-shown structure.
- the unsaturated compound may be a mono-olefin, e.g., hexene-l, decene-l, etc., a cycloolefin such as cyclohexene or cycloheptene, a polyolefin such as polybutadiene or polymeric materials containing ethylenic unsaturation such as polybutenes, and aromatic olefins such as styrene. Also included are unsaturates such as dioctyl maleate, dioctyl fumarate, methyl-lo-undecenoate, and glycerol monooleate. These poly(organo) siloxanes are described in detail in US. application Ser. No. 308,335, filed Sept. 23, 1963, now Pat. No. 3,450,736 dated June 6, 1969.
- dehydrocondensed poly(organo) siloxanes prepared simply by heating the above poly(organo) siloxane with a hydrocarbyl hydroperoxide, a dehydrocarbyl peroxide, an acyl hydroperoxide or a diacyl peroxide.
- a hydrocarbyl hydroperoxide a hydrocarbyl hydroperoxide
- a dehydrocarbyl peroxide a dehydrocarbyl peroxide
- an acyl hydroperoxide or a diacyl peroxide.
- di-tertiary-butyl peroxide is preferred.
- the organophosphine oxide additives of this invention are surprisingly active at low concentrations.
- the most effective concentration thereof in the organic fluid composition will range from about 0.01 to about 10% by weight. Preferably, however, the concentration will range between about 0.03% and 1.0% by weight.
- reaction mixture was then hydrolyzed by adding 1460 m1. of aqueous hydrochloric acid followed by an equal amount of water (1460 ml.
- the reaction mixture was charged to a separatory funnel for settling. The lower aqueous layer was discarded. The upper organic layer was extracted several times with 600 ml. portions of 2% aqueous hydrochloric acid.
- Step (e) of Example 1 Preparation of Steps (a) through (e) of Example 1 were repeated, except that in step (e), after removing the benzene, the diphenylphosphine oxide was topped to 95 C. at 200 mm. of Hg. The yield was 98 g.
- a synthetic base fluid was used.
- the synthetic fluid was a pentaerythritol ester prepared from technical grade pentaerythritol containing about 88% by weight of monopentaerythritol and about 12% by weight of dipentaerythritol, and 4 moles per mole of said pentaerythritol of a mixture of acids consisting of pelargonic acid and commercial iso-pentanoic acid (which contains both normal valeric and iso-valeric acids).
- This synthetic base fluid was tested alone and in combination with each of the compounds of Examples 1 and 2 above at concentrations of 0.04% phosphorus. The following are the results.
- Synthetic fluid 0. 50 0. 72 0. 0. 0. 93 Synthetic fluid plus 0.34% of compound of Example 0. 51 0. 60 Synthetic fluid plus 0.43% of compound of Example 2 0.50 0.55 0.55 0. 60
- An organic fluid composition comprising a major proportion of a lubricating oil and a proportion suflicient to impart load carrying properties thereto of a hydroxysubstituted organo-phosphine oxide of the formula if F (R)2PCR2 wherein R, R and R are hydrocarbyl groups of from 1 to about 30 carbon atoms.
- composition of claim 1 wherein the said organophosphine oxide is present in a concentration of from about 0.01% to about 10% by weight.
- composition of claim 2 wherein the concentration is from about 0.03% to about 1.0% by weight.
- composition of claim 1 wherein the organic fluid is a mineral lubricating oil.
- composition of claim 1 wherein the organic fluid is a synthetic lubricating oil.
- composition of claim 5 wherein the synthetic lubricating oil is a pentaerythritol ester of pelargonic and iso-pentanoic acids.
- composition of claim 1 wherein the said organophosphine oxide is 8.
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Abstract
THE INVENTION PROVIDES LUBRICANT COMPOSITIONS COMPRISING AN ORGANIC FLUID OF LUBRICATIN VISOSITY AND A HYDROXY-SUBSTITUTED ORGANOPHOSPHINE OXIDE. THE COMPOSITION HAS IMPROVED LOAD CARRYING PROPERTIES.
Description
United States Patent ()1 fic'e 3,591,501 LUBRICANT CONTAINING A HYDROXY- SUBSTITUTED PHOSPHINE OXIDE William F. Olszewski, Cherry Hill, N.J., and Herbert Myers, Plymouth Meeting, Pa., assignor to Mobil Oil Corporation No Drawing. Filed Jan. 24, 1969, Ser. No. 793,879 Int. Cl. C10m 1/44 U.S. Cl. 252-493 8 Claims ABSTRACT OF THE DISCLOSURE The invention provides lubricant compositions comprising an organic fluid of lubricating viscosity and a hydroxy-substituted organophosphine oxide. The composition has improved load carrying properties.
BACKGROUND OF THE INVENTION Field of the invention The invention relates to lubricant compositions, and in particular to lubricating compositions comprising an organic fluid of lubricating viscosity and a hydroxy-substituted organophosphine oxide, said composition having improved load carrying properties.
Description of the prior art US. Pat. No. 3,126,416 describes the preparation of hydroxy-substituted organophosphine oxides containing mixed alkyl and aryl groups. Neither this patent, nor any known art discloses the use of the compounds described herein as lubricant additives.
SUMMARY OF THE INVENTION In accordance with the present invention, there is provided an organic fluid composition comprising a major proportion of an organic fluid of lubricating viscosity and a minor proportion suflicient to impart load carrying properties thereto of a hydroxy-substituted organophosphine oxide.
The hydroxy-substituted organophosphine oxide has the formula wherein R, R and R may be the same or different alkyl, cycloalkyl, aralkyl, aryl, alkaryl, and the substituted derivatives thereof, wherein the substituent may be a portion of the ring structure or attached to the alkyl or aryl groups or to either moiety in the alkaryl or aralkyl group, and contain atoms selected from the group consisting of nitrogen, oxygen, sulfur and halogen. In particular, R, R and R are selected from the group consisting of: (a) alkyl, cycloalkyl and heterocyclic groups containing from 1 to about 20 carbon atoms; (b) aryl, aralkyl and alkaryl groups containing a total of from 6 to about 30 carbon atoms; and (c) the substituted members of (a) and (b). The substituent is a member of the group consisting of halogen (chlorine, fluorine, bromine and iodine), hydroxy,
nitro, amino and mercapto when attached as the terminal portions of said groups. Also, the heterocyclic group will contain a substituent from the group consisting of nitrogen, oxygen and sulfur, and the alkyl groups may contain such atoms as portions of the molecule between consecutive atoms in the chain.
The organophosphine oxides of this invention when incorporated with organic fluids, give lubricating compositions having good load carrying properties.
3,591,501 Patented July 6, 1971 DESCRIPTION OF SPECIFIC EMBODIMENTS The secondary organophosphine oxide is then reacted with a ketone to yield the hydroxy-substituted organophosphine oxide substantially as follows:
The diorgano phosphonate used as the starting material for the secondary phosphine oxide may be prepared by reacting an alcohol or a phenol with phosphorus trichloride in the desired mole ratio. For example, the diaryl phosphonates may be prepared by reacting together phenol, water or an alcohol, and phosphorus trichloride in accordance with the method disclosed in US. Pat. No. 3,329,742. The mole ratio of phenol to water or alcohol to phosphorus trichloride is 2 to 1 to 1, and the temperature is within the range of about 25 C. to about C.
As has been stated, the hydroxy-substituted organophosphine oxides disclosed herein are eifective to impart load carrying properties to a variety of organic fluids having lubricating viscosity. These organic fluids include, in addition to mineral oils such as naphthenic and parafiinic mineral oils, synthetic oils including hydrocarbon base fluids, glycol ether fluids, poly(organo) siloxane fluids, acetals, polyphenyl ethers, and the synthetic ester fluids produced from monohydric alcohols and polycarboxylic acids, or from polyhydric alcohols, such as trimethylolpropane and pentaerythritol, and carboxylic acids having up to about 20 carbon atoms.
As an example of the hydrocarbon base fluid, there may be mentioned a polyolefinic fluid or a hydrogenated derivative thereof. One suitable fluid is similar to that disclosed and claimed in US. Pat. 3,149,178. In this patent, the olefinic fluids are polymerized normal alphamonoolefins which are distilled to yield a. dimer fraction and a dimer-free fraction. The dimer-free fraction may be thereafter hydrogenated in the presence of a catalyst, such as boron trifluoride. Other useful olefinic fluids may be prepared in accordance with US. Pat. 3,382,291.
The poly(organo)siloxane fluids may be exemplified by those products obtained by reacting a polysiloxane containing the recurring unit and having a molecular weight of from about 500 to about 10,000 with an unsaturated compound containing at least one double bond; which compound adds to the H of the above-shown structure. The unsaturated compound may be a mono-olefin, e.g., hexene-l, decene-l, etc., a cycloolefin such as cyclohexene or cycloheptene, a polyolefin such as polybutadiene or polymeric materials containing ethylenic unsaturation such as polybutenes, and aromatic olefins such as styrene. Also included are unsaturates such as dioctyl maleate, dioctyl fumarate, methyl-lo-undecenoate, and glycerol monooleate. These poly(organo) siloxanes are described in detail in US. application Ser. No. 308,335, filed Sept. 23, 1963, now Pat. No. 3,450,736 dated June 6, 1969.
Also included among the useful organic fluids are the dehydrocondensed poly(organo) siloxanes, prepared simply by heating the above poly(organo) siloxane with a hydrocarbyl hydroperoxide, a dehydrocarbyl peroxide, an acyl hydroperoxide or a diacyl peroxide. Of the peroxides, di-tertiary-butyl peroxide is preferred.
The organophosphine oxide additives of this invention are surprisingly active at low concentrations. The most effective concentration thereof in the organic fluid composition will range from about 0.01 to about 10% by weight. Preferably, however, the concentration will range between about 0.03% and 1.0% by weight.
The following examples illustrate the preparation of the organophosphine oxides and their utility in imparting load carrying properties to organic fluids.
EXAMPLE 1 Preparation of CH3 (CeHs)2i CCHs (a) Anhydrous diethyl ether (725 ml.) and magnesium metal turnings (88 g., 3.65 moles) were charged to a 5.0 liter reaction flask. A solution of bromobenzene (5 00 g., 3.18 moles) in anhydrous diethyl ether (725 ml.) was added dropwise to the flask over a period of 3 hours at a rate which kept the reaction mixture under gentle reflux. When the addition was completed, the reaction was refluxed for an additional 15 minutes.
(b) The reaction mixture was cooled to 0-10 C. in an ice bath and a solution of diethyl phosphonate (146 g., 1.06 mole) in anhydrous diethyl ether (585 ml.) was added dropwise over a period of 3 hours while maintaining the temperature at 0-10 C. After the addition was completed, the reaction mixture was refluxed for 15 minutes.
(0) The reaction mixture was then hydrolyzed by adding 1460 m1. of aqueous hydrochloric acid followed by an equal amount of water (1460 ml. The reaction mixture was charged to a separatory funnel for settling. The lower aqueous layer was discarded. The upper organic layer was extracted several times with 600 ml. portions of 2% aqueous hydrochloric acid.
(d) The combined hydrochloric acid extracts were in turn extracted with several 400 ml. portions of benzene. The combined benzene extracts were dried over anhydrous sodium sulfate.
(e) After removing the benzene by distillation, the diphenylphosphine oxide was topped to a pot temperature of 90 C. at 5 mm. of Hg and filtered (yield, 70 g.).
(f) The diphenylphosphine oxide and excess acetone (150 g.) were warmed on a steam bath for minutes. Upon cooling, the hydroxy-substituted organophosphine oxide percipitated and was collected by suction filtration (yield, 65 g.).
Product analysis.--Calculated for C14H1102P (percent): phosphorus, 12.5; Chlorine, nil. Found (percent): phosphorus, 11.9; chlorine, nil.
EXAMPLE 2 Preparation of Steps (a) through (e) of Example 1 were repeated, except that in step (e), after removing the benzene, the diphenylphosphine oxide was topped to 95 C. at 200 mm. of Hg. The yield was 98 g.
(f) The diphenylphosphine oxide and excess 2-octanone (150 g.) were warmed on a steam bath for 15 minutes. Upon cooling, the hydroxy-substituted organophosphine oxide precipitated and was Collected by suction filtration (yield, 94 g.).
Product alzalysis.Calculated for C H O P (percent): Phosphorus, 9.4. Found (percent): Phosphorus, 9.4.
EXAMPLE 3 Evaluation of the compounds The above compounds were evaluated in the well-known 4-Ball Wear Test. In this test, three steel balls are held stationary while a fourth steel ball is allowed to rotate thereon under a 60 Kg load for a period of 30 minutes. The temperature of the base fluid and the rotational speed of the fourth ball were varied as shown in the table below.
For the purpose of this test, a synthetic base fluid was used. The synthetic fluid was a pentaerythritol ester prepared from technical grade pentaerythritol containing about 88% by weight of monopentaerythritol and about 12% by weight of dipentaerythritol, and 4 moles per mole of said pentaerythritol of a mixture of acids consisting of pelargonic acid and commercial iso-pentanoic acid (which contains both normal valeric and iso-valeric acids). This synthetic base fluid was tested alone and in combination with each of the compounds of Examples 1 and 2 above at concentrations of 0.04% phosphorus. The following are the results.
Scar diameter (mm.) F.
System r.p.m. r.p.m. r.p.m. r.p.m.
Synthetic fluid. 0. 50 0. 72 0. 0. 93 Synthetic fluid plus 0.34% of compound of Example 0. 51 0. 60 Synthetic fluid plus 0.43% of compound of Example 2 0.50 0.55 0.55 0. 60
It will be noted from the above results that, at the low temperature there is a significant improvement in the performance of the ester at a speed of 500 r.p.m. However, at 390 F., great improvement was noted at all speeds.
While the present invention has been described in considerable detail in connection with a few specific embodiments for specific purposes, it is apparent that novel compositions of this invention are not restricted to such embodiments and details for there are many obvious modifications and variations which enhance their wide application in various types of utilization. Accordingly, the present invention should not be construed as limited in any particulars except as may be recited in the appended claims or required by the prior art.
We claim:
1. An organic fluid composition comprising a major proportion of a lubricating oil and a proportion suflicient to impart load carrying properties thereto of a hydroxysubstituted organo-phosphine oxide of the formula if F (R)2PCR2 wherein R, R and R are hydrocarbyl groups of from 1 to about 30 carbon atoms.
2. The composition of claim 1 wherein the said organophosphine oxide is present in a concentration of from about 0.01% to about 10% by weight.
3. The composition of claim 2 wherein the concentration is from about 0.03% to about 1.0% by weight.
4. The composition of claim 1 wherein the organic fluid is a mineral lubricating oil.
5. The composition of claim 1 wherein the organic fluid is a synthetic lubricating oil.
6. The composition of claim 5 wherein the synthetic lubricating oil is a pentaerythritol ester of pelargonic and iso-pentanoic acids.
7. The composition of claim 1 wherein the said organophosphine oxide is 8. The composition of claim 1 wherein the said organo- References Cited UNITED STATES PATENTS O DANIEL E. WYMAN, Primary Examiner W. H. CANNON, Assistant Examiner US. Cl. X.R.
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Application Number | Priority Date | Filing Date | Title |
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US79387969A | 1969-01-24 | 1969-01-24 |
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US3591501A true US3591501A (en) | 1971-07-06 |
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US793879*A Expired - Lifetime US3591501A (en) | 1969-01-24 | 1969-01-24 | Lubricant containing a hydroxy-substituted phosphine oxide |
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3932290A (en) * | 1973-10-04 | 1976-01-13 | The Lubrizol Corporation | Phosphorus-containing friction modifiers for functional fluids |
US4474675A (en) * | 1982-12-20 | 1984-10-02 | Fmc Corporation | Phosphine oxides for use as functional fluids |
US5288418A (en) * | 1992-12-03 | 1994-02-22 | Mobil Oil Corporation | Amine-coupled hindered phenols and phosphites as multifunctional antioxidant/antiwear additives |
WO2020175634A1 (en) * | 2019-02-28 | 2020-09-03 | 国立研究開発法人産業技術総合研究所 | Method for producing organophosphorus compound |
CN114773282A (en) * | 2022-05-27 | 2022-07-22 | 杭州布朗生物医药科技有限公司 | Preparation method of 3-tert-butyl-6-ethylthio-1, 3, 5-triazine-2, 4(1H,3H) -diketone |
-
1969
- 1969-01-24 US US793879*A patent/US3591501A/en not_active Expired - Lifetime
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3932290A (en) * | 1973-10-04 | 1976-01-13 | The Lubrizol Corporation | Phosphorus-containing friction modifiers for functional fluids |
US4474675A (en) * | 1982-12-20 | 1984-10-02 | Fmc Corporation | Phosphine oxides for use as functional fluids |
US5288418A (en) * | 1992-12-03 | 1994-02-22 | Mobil Oil Corporation | Amine-coupled hindered phenols and phosphites as multifunctional antioxidant/antiwear additives |
WO2020175634A1 (en) * | 2019-02-28 | 2020-09-03 | 国立研究開発法人産業技術総合研究所 | Method for producing organophosphorus compound |
CN113474350A (en) * | 2019-02-28 | 2021-10-01 | 国立研究开发法人产业技术综合研究所 | Process for producing organic phosphorus compound |
CN114773282A (en) * | 2022-05-27 | 2022-07-22 | 杭州布朗生物医药科技有限公司 | Preparation method of 3-tert-butyl-6-ethylthio-1, 3, 5-triazine-2, 4(1H,3H) -diketone |
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